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A kind of preparation method of 2-arylquinoline derivatives

An arylquinoline and derivative technology, which is applied in the field of preparation of 2-arylquinoline derivatives, can solve the problems of expensive aryl source substrates or catalysts, limited scope of application of substrates, harsh reaction conditions, and the like, Achieving the effect of high yield, easy operation and mild reaction conditions

Active Publication Date: 2019-02-26
HENAN UNIVERSITY OF TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although these methods can synthesize 2-arylquinoline derivatives, there are still some problems: the price of the aryl source substrate or catalyst used is relatively expensive, the reaction conditions are relatively harsh, the reaction time is long, and the scope of application of the substrate is limited.

Method used

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  • A kind of preparation method of 2-arylquinoline derivatives
  • A kind of preparation method of 2-arylquinoline derivatives
  • A kind of preparation method of 2-arylquinoline derivatives

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Example 1.R 1 =-CH 3 , R 2 = R 3 When =-H, the preparation of 2-phenyl-4-methylquinoline derivatives

[0032] Add 4-methylquinoline (0.5mmol, 71.5mg) and benzoic acid (1.0mmol, 122mg) in a 50mL round bottom flask, then add the catalyst AgNO 3 (0.05mmol, 8.5mg), oxidant K 2 S 2 o 8 (1.5mmol, 405mg), trifluoroacetic acid (0.5mmol, 72mg) as auxiliary agent and 5.0mL acetonitrile as solvent, reflux reaction at 90°C for 8.0h; NaHCO 3 The solution was neutralized to neutral, extracted twice with 15mL ethyl acetate, and the extract was washed twice with saturated brine; the extract was washed with anhydrous Na 2 SO 4 After drying and concentration under reduced pressure, it was separated and purified by column chromatography (eluent: ethyl acetate / petroleum ether=1 / 15) to obtain 0.083 g of a yellow viscous liquid with a yield of 76.0%.

[0033]

[0034] yellow viscous liquid; 1 H NMR (400MHz, CDCl 3 )δ:8.24(d,J H-H =8.4Hz,1H),8.16(d,J H-H =7.2Hz, 1H), 7.75-7.7...

Embodiment 2

[0035] Example 2.R 1 =-CH 3 , R 2 =-H, R 3 =-OCH 3 , the preparation of 2-(4-methoxyphenyl)-4-methylquinoline derivatives

[0036]Add 4-methylquinoline (0.5mmol, 71.5mg) and 4-methoxybenzoic acid (1.0mmol, 152mg) in 50mL round bottom flask, then add catalyst AgNO 3 (0.05mmol, 8.5mg), oxidant K 2 S 2 o 8 (1.5mmol, 405mg), trifluoroacetic acid (0.5mmol, 72mg) as auxiliary agent and 5.0mL water as solvent, reflux reaction at 100°C for 10.0h; after the reaction, add 5.0mL ethyl acetate, then filter to remove insoluble , add saturated NaHCO to the filtrate 3 The solution was neutralized to neutral, extracted twice with 15mL ethyl acetate, and the extract was washed twice with saturated brine; the extract was washed with anhydrous Na 2 SO 4 After drying and concentration under reduced pressure, it was separated and purified by column chromatography (eluent: ethyl acetate / petroleum ether=1 / 15) to obtain 0.097 g of a yellow viscous liquid with a yield of 78.0%.

[0037] ...

Embodiment 3

[0039] Example 3.R 1 =-CH 3 , R 2 =-H, R 3 When =-F, the preparation of 2-(4-fluorophenyl)-4-methylquinoline derivatives

[0040] Add 4-methylquinoline (0.5mmol, 71.5mg) and 4-fluorobenzoic acid (1.0mmol, 140mg) in a 50mL round bottom flask, then add the catalyst AgNO 3 (0.05mmol, 8.5mg), oxidant K 2 S 2 o 8 (1.5mmol, 405mg), trifluoroacetic acid (0.5mmol, 72mg) as auxiliary agent and 3.0mL acetonitrile and 3.0mL water as mixed solvent, reflux reaction at 100°C for 9.0h; after the reaction, add 5.0mL ethyl acetate , and then filtered to remove insoluble matter, and saturated NaHCO was added to the filtrate 3 The solution was neutralized to neutral, extracted twice with 15mL ethyl acetate, and the extract was washed twice with saturated brine; the extract was washed with anhydrous Na 2 SO 4 After drying and concentration under reduced pressure, it was separated and purified by column chromatography (eluent: ethyl acetate / petroleum ether=1 / 10) to obtain 0.089 g of a yel...

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PUM

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Abstract

The invention discloses a preparation method of 2-aryl quinoline derivatives (I), belonging to the field of organic chemistry. The method takes substituted quinoline derivatives and substituted aryl formic acid as raw materials, and comprises the step of enabling K2S2O8 taken as an oxidizing agent and trifluoroacetic acid (TFA) used as an auxiliary agent to be subjected to a reaction in a solvent under the catalytic action of AgNO3 to synthesize the 2-aryl quinoline derivatives, wherein the reaction temperature is 60-100 DEG C, and the reaction time is 6-10 hours. Compared with the existing synthesis method, the preparation method has the advantages that (1) the substituted quinoline derivatives and the substituted aryl formic acid which are low in price and easy to obtain are taken as the raw materials for synthesizing the 2-aryl quinoline in one step, so that the method is low in cost and has good application prospect; (2) the reaction conditions are mild, the reaction is carried out under the condition of air, and the method is high in yield, convenient to operate and the like, so that industrial production is facilitated to be realized. The 2-aryl quinoline derivatives have potential application prospection in the fields such as materials, chemical industry and medicines; the invention provides a new way for synthesizing the 2-aryl quinoline derivatives. The reaction formula is shown in the description.

Description

technical field [0001] The invention relates to a preparation method of 2-arylquinoline derivatives, belonging to the field of organic synthesis. Background technique [0002] Quinoline is an important nitrogen-containing heterocyclic compound, an important structural unit in natural products and medicines, and has significant biological activities such as sterilization, anti-allergy, anti-depression, anti-tumor and anti-cancer. In addition, the arylated derivatives of quinoline are the precursors of many drugs and are valuable molecular building blocks in organic synthesis, functional materials, and pharmacology due to their unique physical properties and biological activities. contain this important structure. Therefore, it is of great research value to carry out the synthesis of quinoline arylation derivatives. [0003] (a) [0004] [0005] (b) [0006] [0007] 2-Arylquinoline derivatives are an important class of quinoline derivatives. In recent years, the re...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D215/04C07D215/14C07D215/12C07D215/20C07D215/18
CPCC07D215/04C07D215/12C07D215/14C07D215/18C07D215/20
Inventor 袁金伟杨亮茹买文鹏肖咏梅游利琴毛璞尹秋月屈凌波
Owner HENAN UNIVERSITY OF TECHNOLOGY